“If the shoe fits, wear it” are words to live by. But when that living takes place in cooler months, there’s always a middle step: check the weather, because no matter how cute those mules are, you’re not going to feel so hot when walking through rain or snow.

And since cold weather doesn’t have to mean lukewarm looks, we partnered with Sperry to see how 3 fashion pros—Emilia MusacchiaTally Dilbert, and Lindsay Stevens—are creating chic looks with their all-weather, all-style boots. (We also want you to look hot AF when it’s cold AF, so here’s 15% off your inevitable order of Sperrys.)*

 

When it comes to the Musacchia clan, fashion is a family affair. Emilia (she / her) currently runs Eveliina Vintage with her twin sister, but the shop was founded by her mom Eva back in the ‘70s. “We were my mom’s models and muses,” she explains. “At first, my sister and I hated it. We were like, ‘These clothes smell bad and they’re old!’” But since what’s in is never out for long, Emilia is using all those “old, smelly” clothes to become a style powerhouse online and IRL.

“My style is whatever I’m feeling that day,” she says while sitting in front of a rack stocked with mid-century pastel garments. One day she’s mix-matching patterns, another she’s going for “Alexa Chung chic.” “I don’t look at trends, but I want to be comfortable, cute, and weather-appropriate. Those are my 3 rules when getting dressed.” When the weather calls for water-resistant shoes, the New Yorker laces up her Sperrys to make sure her style (and feet) don’t slip.

“When I was in high school, one of my friends always wore clothes so beautifully, and then she would wear her Sperry boots,” she recalls. “I’ve loved it ever since I saw the silhouette. You can wear them with a short, neutral dress or a sweater and some trousers—so many different ways.” That takes care of the cute, and Emilia says her Sperrys’ supportive sole and weather-proofing takes care of the comfortable. “In New York, everything needs to be thought out and chic, so with my Sperry boots, I can walk outside, my feet aren’t going to get wet, and they’re cute. They can go fashion; they can go function.”

 

As a freelance social media manager, influencer, and part-time artist, Tally Dilbert (she / her) lives with her boots on the ground. “I’m always out in the city because I work with different brands locally and outside [of Texas].” She’s “always creating content,” which translates to always having to look content-ready. “My style overall is very versatile. I like to try new things from the chicest style to grunge to street,” she says. While Tally has a soft spot for earth tones, she has a firm position when it comes to assembling winter ‘fits.

“Normally I go with sneakers, but when it rains, they get soaked,” she explains. “My Sperry boots make it faster for me to get stuff done because I feel comfortable. They’re black with a purple sole, so I do neutral colors, styling it with either leather pants or jeans or a black skirt.”

Once her look is locked, it’s time to see if it holds up to whatever the heavens bring. And since a day of Tally-testing means running around Texas like a woman with her Wi-Fi cut off, she says it’s vetted for staying warm on the go, and apparently, trudging through sticky spots on the bar floor. (Modelo is for your glass or your mouth, people, not our shoes.)

 

“I’ve always been into the outdoors,” says Lindsay (she / her). “I grew up going camping and hiking with my family in San Diego. When I got older, I noticed I was always going with my guy friends.” Of course, Lindsay knew there were other women who loved a 9-mile trek just as much as she did, so last year, she founded Outdoorsy Gals, “a community to plan meetups and trips with other adventurous women all over the world.”

And while you’d think she stays in athleisure 24 / 7, a few years of New York life shaped her self-described classic style. “As soon as I’m done backpacking, I’ll put on a beautiful flowy sundress, or a cute sweater with dangly earrings, jeans, and my Sperry boots,” Lindsay says.

Before NY, she picked up some fashion tips in Richmond. “Sperrys were so popular over there [that] I fell in love with them,” she remembers. “Now, I’m traveling constantly. I have limited space in my suitcase, so I need something that’s going to work for a lot of different situations. Sperrys are ideal because I can wear them hiking because of the waterproofing on the bottom, but I can also wear them to a nice dinner with straight-leg jeans, a chunky fall jacket, and gold hoop earrings.”

*Means this is a sponsored section.